Condensed bicyclic heterocyclic derivatives as pest control agents

Abstract

The invention relates to novel compounds of formula (I), in which Aa, Ab, Ac, Ad, Ae, Q, R 1 and n are defined as in the description, to the use thereof as acaricides and/or insecticides for controlling animal pests, and to processes and intermediate products for the preparation thereof.

The invention claimed is: 
     
       1. A compound of formula (I) 
       
         
           
           
               
               
           
         
         wherein 
         Aa represents nitrogen or =C(R 7 )—, 
         Ab represents nitrogen or =C(R 8 )—, 
         Ac represents nitrogen or =C(R 9 )—, 
         Ad represents nitrogen or =C(R 10 )—, 
         Ae represents nitrogen or =C(R 11 )—, 
         wherein Ab, Ac, Ad and Ae cannot simultaneously represent nitrogen, 
         resulting in the following structural units: A1, A2, A6, A11, or A16, 
         R 1  represents (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl or (C 3 -C 6 )-cycloalkyl, 
         R 7  represents hydrogen, halogen, cyano, (C 1 -C 4 )-alkyl or (C 1 -C 4 )-haloalkyl, 
         R 8 , R 10 , R 11  independently of one another represent hydrogen, (C 1 -C 4 )-alkyl or halogen, 
         R 9  represents cyano (C 3 -C 6 ) cycloalkyl, 
         wherein only one or two of the radicals R 8 , R 9 , R 10 , R 11  represent a substituent other than hydrogen, 
         Q is represented by Q1, Q4, Q10, Q11, Q14, Q15, Q19, Q20 or Q21, 
       
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         R 4  represents (C 1 -C 4 )-alkyl or (C 1 -C 4 )-alkoxy-(C 1 -C 4 )-alkyl, 
         R 5  represents hydrogen, cyano, halogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl, (C 3 -C 6 )-cycloalkyl, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-haloalkoxy, (C 1 -C 4 )-alkoxyimino, (C 1 -C 4 )-alkylthio, (C 1 -C 4 )-haloalkylthio, (C 1 -C 4 )-alkylsulfinyl, (C 1 -C 4 )-haloalkylsulfinyl, (C 1 -C 4 )-alkylsulfonyl, (C 1 -C 4 )-haloalkylsulfonyl, (C 1 -C 4 )-alkylcarbonyl or (C 1 -C 4 )-haloalkylcarbonyl, 
         R 6  represents hydrogen, 
         R 6a  represents (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl, (C 2 -C 4 )-alkenyl, (C 2 -C 4 )-haloalkenyl, (C 1 -C 4 )-alkoxy-(C 1 -C 4 )-alkyl, (C 2 -C 4 )-alkynyl, (C 2 -C 4 )-haloalkynyl or (C 3 -C 6 )-cycloalkyl, 
         and 
         n represents 0, 1 or 2. 
       
     
     
       2. The compound of  claim 1  wherein
 Aa represents ═C(R 7 )—, 
 Ab represents ═C(R 8 )—, 
 Ac represents ═C(R 9 )—, 
 Ad represents ═C(R 10 )—, 
 Ae represents ═C(R 11 )—, 
 R 1  represents methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl or tert-butyl, 
 R 7  represents hydrogen, 
 R 8  represents hydrogen, 
 R 9  represents cyanocyclopropyl or cyanocyclobutyl, 
 R 10  represents hydrogen, 
 R 11  represents hydrogen, 
 Q represents Q1, Q4, or Q21, 
 R 4  represents methyl, ethyl, isopropyl, methoxymethyl or methoxyethyl, 
 R 5  represents fluorine, chlorine, bromine, fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl (CH 2 CFH 2 , CHFCH 3 ), difluoroethyl (CF 2 CH 3 , CH 2 CHF 2 , CHFCFH 2 ), trifluoroethyl, (CH 2 CF 3 , CHFCHF 2 , CF 2 CFH 2 ), tetrafluoroethyl (CHFCF 3 , CF 2 CHF 2 ), pentafluoroethyl, trifluoromethoxy, pentafluoroethoxy, difluorochloromethoxy, dichlorofluoromethoxy, trifluoromethylthio, trifluoromethylsulfinyl or trifluoromethylsulfonyl, 
 R 6  represents hydrogen, 
 R 6a  represents methyl, and 
 n represents 0, 1 or 2. 
 
     
     
       3. The compound of  claim 1  wherein
 Aa represents ═C(R 7 )—, 
 Ab represents ═C(R 8 )—, 
 Ac represents ═C(R 9 )—, 
 Ad represents ═C(R 10 )—, 
 Ae represents ═C(R 11 )—, 
 R 1  represents ethyl, 
 R 7  represents hydrogen, 
 R 8  represents hydrogen, 
 R 9  represents 1-cyanocyclopropyl, 
 R 10  represents hydrogen, 
 R 11  represents hydrogen, 
 Q represents Q1, Q4, or Q21, 
 R 4  represents methyl, 
 R 5  represents trifluoromethyl, pentafluoroethyl, trifluoromethoxy, pentafluoroethoxy or trifluoromethylsulfonyl, 
 R 6  represents hydrogen, 
 R 6a  represents methyl, and 
 n represents 2. 
 
     
     
       4. The compound of  claim 1 , wherein
 Aa represents nitrogen or =C(R 7 )—, 
 Ab represents nitrogen or =C(R 8 )—, 
 Ac represents nitrogen or =C(R 9 )—, 
 Ad represents nitrogen or =C(R 10 )—, 
 Ae represents nitrogen or =C(R 11 )—, 
 wherein Ab, Ac, Ad and Ae cannot simultaneously represent nitrogen, 
 resulting in the structural unit: A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16, or A17. 
 
     
     
       5. The compound of  claim 1 , wherein
 Aa represents nitrogen or =C(R 7 )—, 
 Ab represents nitrogen or =C(R 8 )—, 
 Ac represents nitrogen or =C(R 9 )—, 
 Ad represents nitrogen or =C(R 10 )—, 
 Ae represents nitrogen or =C(R 11 )—, 
 wherein Ab, Ac, Ad and Ae cannot simultaneously represent nitrogen, 
 resulting in the structural unit: A1, A2, A6, A7, A9, A11, A13, or A16. 
 
     
     
       6. The compound of  claim 1 , wherein
 Aa represents ═C(R 7 )—, 
 Ab represents ═C(R 8 )—, 
 Ac represents ═C(R 9 )—, 
 Ad represents ═C(R 10 )—, 
 Ae represents ═C(R 11 )—, 
 R 1  represents ethyl, 
 R 7  represents hydrogen, 
 R 8  represents hydrogen, 
 R 9  represents 1-cyanocyclopropyl 
 R 10  represents hydrogen, 
 R 11  represents hydrogen, 
 Q is Q1, 
 R 4  represents methyl, 
 R 5  represents trifluoromethyl, pentafluoroethyl, trifluoromethoxy, pentafluoroethoxy or trifluoromethylsulfonyl, 
 R 6  represents hydrogen, and 
 n represents 2. 
 
     
     
       7. The compound of  claim 1 , wherein
 Aa represents ═C(R 7 )—, 
 Ab represents ═C(R 8 )—, 
 Ac represents ═C(R 9 )—, 
 Ad represents ═C(R 10 )—, 
 Ae represents ═C(R 11 )—, 
 R 1  represents ethyl, 
 R 7  represents hydrogen, 
 R 8  represents hydrogen, 
 represents 1-cyanocyclopropyl, 
 R 10  represents hydrogen, 
 R 11  represents hydrogen, 
 Q is Q4, 
 R 4  represents methyl, 
 R 5  represents trifluoromethyl, pentafluoroethyl, trifluoromethoxy, pentafluoroethoxy or trifluoromethylsulfonyl, 
 R 6  represents hydrogen, and 
 n represents 2. 
 
     
     
       8. The compound of  claim 1 , wherein
 Aa represents ═C(R 7 )—, 
 Ab represents ═C(R 8 )—, 
 Ac represents ═C(R 9 )—, 
 Ad represents ═C(R 10 )—, 
 Ae represents ═C(R 11 )—, 
 R 1  represents ethyl, 
 R 7  represents hydrogen, 
 R 8  represents hydrogen, 
 R 9  represents 1-cyanocyclopropyl, 
 R 10  represents hydrogen, 
 R 11  represents hydrogen, 
 Q is Q21, 
 R 4  represents methyl, 
 R 5  represents trifluoromethyl, pentafluoroethyl, trifluoromethoxy, pentafluoroethoxy or trifluoromethylsulfonyl, 
 R 6  represents hydrogen, 
 R 6a  represents methyl, and 
 n represents 2. 
 
     
     
       9. An agrochemical formulation comprising one or more compounds of  claim 1  and one or more extenders and/or surfactants. 
     
     
       10. A method of controlling one or more animal pests, comprising administering a formulation of  claim 9  on or around a plant and allowing the agrochemical formulation of  claim 7  to act on the animal pests and/or a habitat thereof. 
     
     
       11. The agrochemical formulation as claimed in  claim 9 , additionally comprising a further agrochemically active compound. 
     
     
       12. A method of controlling one or more animal pests, comprising administering a compound of  claim 3  on or around a plant and allowing a compound of  claim 3  to act on the animal pests and/or a habitat thereof. 
     
     
       13. The method of  claim 12  wherein the administering comprises dipping, spraying, evaporating, fogging, scattering, painting on, injecting, or a combination thereof. 
     
     
       14. The method of  claim 4  wherein the administering comprises dipping, spraying, evaporating, fogging, scattering, painting on, injecting, or a combination thereof.